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WO2010076009A1 - Dérivés de pyrimidine et leur utilisation pour lutter contre la croissance indésirable de plantes - Google Patents

Dérivés de pyrimidine et leur utilisation pour lutter contre la croissance indésirable de plantes Download PDF

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Publication number
WO2010076009A1
WO2010076009A1 PCT/EP2009/009287 EP2009009287W WO2010076009A1 WO 2010076009 A1 WO2010076009 A1 WO 2010076009A1 EP 2009009287 W EP2009009287 W EP 2009009287W WO 2010076009 A1 WO2010076009 A1 WO 2010076009A1
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Prior art keywords
alkyl
haloalkyl
compounds
general formula
group
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PCT/EP2009/009287
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German (de)
English (en)
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WO2010076009A8 (fr
Inventor
Klemens Minn
Hansjörg Dietrich
Jan Dittgen
Dieter Feucht
Isolde HÄUSER-HAHN
Christopher Hugh Rosinger
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Bayer Cropscience Ag
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Application filed by Bayer Cropscience Ag filed Critical Bayer Cropscience Ag
Priority to AU2009335286A priority Critical patent/AU2009335286A1/en
Priority to CA2748577A priority patent/CA2748577A1/fr
Priority to EP09799289.5A priority patent/EP2384322B1/fr
Priority to JP2011543990A priority patent/JP5826633B2/ja
Priority to MX2011006278A priority patent/MX2011006278A/es
Priority to BRPI0923893-0A priority patent/BRPI0923893B1/pt
Priority to CN200980153524.1A priority patent/CN102272107B/zh
Publication of WO2010076009A1 publication Critical patent/WO2010076009A1/fr
Publication of WO2010076009A8 publication Critical patent/WO2010076009A8/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/48—Two nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
    • C07D239/50—Three nitrogen atoms

Definitions

  • the invention relates to the technical field of pesticides, in particular that of herbicides for the selective control of weeds and grass weeds in crops.
  • EP 0 523 533 A1 describes substituted 4-aminopyrimidines and their use in the field of crop protection.
  • WO 2008/043031 discloses (R) -6-chloro-N 4 - (8-fluorochroman-4-yl) pyrimidine-2,4,5-triamine as precursor for the preparation of pharmacologically active purines.
  • pyrimidine derivatives which are used as herbicides or plant growth regulators.
  • gulatoren in particular with a satisfactory herbicidal activity against harmful plants, with a broad spectrum against harmful plants and / or with a high selectivity in crops can be used.
  • These pyrimidine derivatives should preferably have a better property profile, in particular a better herbicidal action against harmful plants, a broader spectrum of harmful plants and / or a higher selectivity in crops than the pyrimidine derivatives known from the prior art.
  • new pyrimidines have now been found which can be used advantageously as herbicides and plant growth regulators.
  • the compounds of this series are distinguished not only by good activity profile and crop plant compatibility, but also by cost-effective production processes and access possibilities, since the substances according to the invention can be prepared from inexpensive and easily accessible precursors and therefore to the
  • the present invention therefore relates to compounds of the formula (I) and their salts
  • R 1 and R 2 are selected from the group consisting of Hydrogen, halogen, hydroxy, cyano, nitro, amino, C (O) OH, C (O) NH 2 ;
  • C 6 haloalkenylcarbonyl, (C 2 -C 6 ) alkenyloxy, (C 2 -C 6 ) haloalkenyloxy, (C 2 -C 6 ) alkenyloxycarbonyl, (C 2 -C 6 ) haloalkenyloxycarbonyl; (C 2 -C 6) -alkynyl, (C 2 -C 6) -haloalkynyl, (C 2 -C 6) -alkynylcarbonyl, (C 2 - C 6) -Haloalkinylcarbonyl, (C 2 -C 6) alkynyloxy, (C 2 -C 6 ) -haloalkynyloxy, (C 2 -C 6 ) -alkynyloxycarbonyl, (C 2 -C 6 ) -haloalkynyloxycarbonyl;
  • (C 1 -C 6 ) -alkyl and / or halogen may be substituted; (C 3 -C 8 ) -cycloalkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (Cs-C 1 -C 6 -cycloalkyKd-C 6 ) -haloalkyl, (Cs-CjO-cycloalkyKCrCeO -alkoxy, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 6 ) -haloalkoxy, (C 3 -C 8 ) -cycloalkylcarbonyl, (C 3 -C 8 ) -cycloalkoxycarbonyl, (C 3 -C 8 ) -Cycloalkyl- (C 1 -C 6 ) -alkylcarbonyl, (C 3 -C 8 ) -Cycloal
  • Haloalkylsulfonyl (dC ⁇ -haloalkylthio, (C 1 -C 6) - haloalkylsulfinyl, (C 1 -C 6) alkylsulphonyl (C 1 -C 6) alkyl, (C 1 -C 6) - Alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfinyl (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyKCi-CeJ-alkylCrCeJ-haloalkylthio-Cd-CeJ-alkyl, (C 1 -C 6) - Haloalkylsulfinyl- (C 1 -C 6) alkyl l (C 1 -C 6) alkylsulphonyl (C 1 -C
  • R 3 is selected from the group consisting of hydrogen, (C 1 -C 6 ) alkyl and (dC 6 ) haloalkyl;
  • R 4 and R 5 are selected from the group consisting of hydrogen, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl,
  • R 7 each independently, are selected from the group consisting of hydrogen, (CrC 6) alkyl, (dC 6) -haloalkyl, (C 1 -C 6) - Alkoxy, (CrC 6) -haloalkoxy, (C 6 -C 4) -aryl, (C 6 -C 14) aryloxy, (C 6 - C 4) arylcarbonyl and (C 6 -C 14) aryloxycarbonyl; or the radicals R 6 and R 7 together form a (C 2 -C 7 ) -alkylene group, which may contain one or more oxygen and / or sulfur atoms, wherein the (C 2 -C 7 ) -alkylene group by halogen singly or multiply may be substituted and the respective halogen substituents may be identical or different,
  • R 8 , R 9 , R 10 and R 11 are each selected from the group consisting of hydrogen, halogen, cyano, nitro, (C 1 -
  • X is a bond, CH 2 , O, S, carbonyl, NH, CR 12 Ri 3 and NR 14 ,
  • R 12 R 13 are each independently selected from the group consisting of hydrogen, (C r C6) alkyl, (Ci-C 6) -haloalkyl,
  • R 14 is selected from the group consisting of hydrogen, (C 1 -C 6 ) -
  • R 1 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 or R 11 is other than hydrogen when R 2 is CF 3
  • R 2 is not chlorine when R 1 is NH 2 .
  • the compounds according to the invention differ from the compounds according to EP 0 523 533 A1 in that they are bicyclically substituted 4-aminopyrimidine-2-amines. According to the invention, it has been found that these compounds have a good activity profile and crop plant compatibility. In the following, preferred, particularly preferred and very particularly preferred meanings for the individual substituents will now be described.
  • a first embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 1 is particularly preferably selected from the group consisting of hydrogen, cyano, fluorine, chlorine, bromine, iodine, nitro, trimethylsilylethynyl, methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, n-pentyl, n-heptyl , Cyclopropyl, cyclobutyl, acetyl, ethynyl, amino, dimethylamino,
  • Trifluoromethyl difluoromethyl, monofluoromethyl, methoxy, ethoxy and methoxymethyl
  • R 1 is very particularly preferably cyano, acetyl or trifluoromethyl.
  • a second embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 2 is preferably selected from the group consisting of hydrogen, halogen, (C 1 -C 6 ) -alkylphenyl, (C 6 -C 4 ) -aryl, which is bonded to the aryl radical by (C 1 -)
  • C 6 ) alkyl, (C 6 -C 14 ) haloalkyl and / or halogen may be substituted; C 6 -aryl (CrC 6) -haloalkyl, (Ci-C 6) -alkyl, (d-CeJ-HaloalkyUd-CeJ-alkoxy, (C 1 -C 6) - Alkoxy (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl which may be substituted by (Ci- C 6) alkyl, (C 6 -C 4) haloaryl and / or halogen on the cycloalkyl radical ; 1- (C 1 -C 6 ) -alkylcyclopropyl, 1 - ((C 1 -C 6 ) -alkyl-C 6 -aryl) -cyclopropyl, 1- (monohalophenyl) -cyclopropyl, 1 -
  • R 2 is particularly preferably selected from the group consisting of
  • R 2 is very particularly preferably hydrogen, methyl or difluoromethyl.
  • a third embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 1 and R 2 together with the carbon atoms to which they are attached preferably form a five- or six-membered ring which may be interrupted by one or two heteroatoms selected from the group consisting of oxygen and sulfur;
  • a fourth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 3 is preferably hydrogen or (C 1 -C 6 ) alkyl
  • R 3 is particularly preferably hydrogen.
  • a fifth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 4 and R 5 are preferably selected from the group consisting of hydrogen, (C 1 -C 6) -alkyl, hydroxy,
  • R 4 and R 5 are each independently selected, more preferably selected from the group consisting of hydrogen, methyl, ethyl, propyl,
  • R 4 and R 5 are each independently, most preferably methyl, ethyl or hydrogen.
  • R 4 and R 5 are hydrogen. It is further preferred if at least one of the radicals R 4 or R 5 is hydrogen and the other radical R 4 or R 5 is other than hydrogen, in particular (C 1 -C 6 -alkyl.
  • one of the radicals R 4 or R 5 is hydrogen and the other radical of R 4 or R 5 is methyl.
  • a sixth embodiment of the present invention comprises compounds of the general formula (I) in which R 4 and R 5 preferably together form a (C 2 -C 7 ) -alkylene group which may contain one or more oxygen and / or sulfur atoms, wherein the (C 2 -C 7 ) -alkylene group may be monosubstituted or polysubstituted by halogen and the respective halogen substituents may be the same or different; and
  • R 4 and R 5 are more preferably -CH 2 -CH 2 -CH 2 - or -CH 2 -CH 2 -.
  • a seventh embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 6 and R 7 are preferably selected from the group consisting of hydrogen, (C 1 -C 6 ) -alkyl and (C 6 -C 14 ) -aryl;
  • R 6 and R 7 independently of one another, are more preferably selected from the group consisting of hydrogen, methyl and phenyl;
  • R 6 and R 7 are very particularly preferably hydrogen.
  • An eighth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 8 is preferably selected from the group consisting of hydrogen, (C 1 -C 6 ) -alkyl or halogen;
  • R 8 is more preferably selected from the group consisting of hydrogen, methyl or fluorine
  • R 8 is very particularly preferably hydrogen.
  • a ninth embodiment of the present invention includes compounds of the general formula (I) in which
  • R 9 is preferably selected from the group consisting of hydrogen and (C 1 -C 6 ) -alkyl
  • R 9 is more preferably selected from the group consisting of hydrogen and methyl
  • R 9 is very particularly preferably hydrogen.
  • a tenth embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 10 is preferably selected from the group consisting of hydrogen, (Cr C 6) alkyl, di- (Ci-C 6) alkylamino, halogen, (C 2 -C 6) alkenyl, (C 2 -C 6 ) -alkynyl,
  • R 10 is particularly preferably selected from the group consisting of hydrogen, methyl, propyl, isopropyl, butyl, tert-butyl, dimethylamino, fluorine, chlorine,
  • R 10 is very particularly preferably hydrogen or methyl.
  • An eleventh embodiment of the present invention comprises compounds of the general formula (I) in which
  • R 11 is preferably selected from the group consisting of hydrogen and (C 1 -C 6) -alkyl; R 11 is more preferably selected from the group consisting of hydrogen and methyl; and
  • R 11 is very particularly preferably hydrogen.
  • a twelfth embodiment of the present invention comprises compounds of the general formula (I) in which
  • X is preferably selected from the group consisting of CH 2 , O, NH, a chemical bond and S;
  • X is more preferably selected from the group consisting of CH 2 and O and a chemical bond.
  • the compound of the general formula (I) also includes compounds which are quaternized by a) protonation, b) alkylation or c) oxidation on a nitrogen atom.
  • the compounds of formula (I) can form salts.
  • (I) carried an acidic hydrogen atom, for example, in the case that R 1 contains a COOH group or a sulfonamide group -NHSO 2 -.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and KaIi- umcarbonat and sodium and potassium bicarbonate.
  • salts are compounds in which the acidic hydrogen is replaced by an agriculturally suitable cation, for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts with, for example, cations of the formula [NRR ' R ' R '' ] where R 1 to R ''' each independently of one another are an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl. such as (C 1 -C 4 ) -trialkylsulfonium and (C 1 -C 4 ) -trialkylsulfoxonium salts.
  • an agriculturally suitable cation for example metal salts, in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or else ammonium salts, salts with organic amines or quaternary (
  • the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids are present, inner salts with their turn protonatable groups, such as amino groups form.
  • these radicals are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, or in unsaturated groups having 2 to 6 carbon atoms, in particular 2 to 4 carbon atoms, is preferred.
  • Alkyl radicals including in the composite meanings such as alkoxy, haloalkyl, etc., mean, for example, methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i -Hexyl and 1, 3-dimethylbutyl, heptyls such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals; wherein at least one double bond or triple bond, preferably a double bond or triple bond is included.
  • Alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, but-3-ene-1 -yl, 1-methylbut-3-en-1-yl and 1-methyl-but-2-en-1-yl;
  • Alkynyl means, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl and 1-methyl-but-3-yn-1-yl.
  • Cycloalkyl groups are, for. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.
  • the cycloalkyl groups can occur in bi- or tri-cyclic form.
  • haloalkyl groups and haloalkyl groups of haloalkoxy, haloalkylthio, haloalkenyl, haloalkynyl and the like are mentioned. are indicated in these residues, the lower carbon skeletons, z. B. with 1 to 6 carbon atoms or 2 to 6, in particular 1 to 4 carbon atoms or preferably 2 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton in each case straight-chain or branched. Examples are difluoromethyl, 2,2,2-trifluoroethyl, trifluoroallyl, 1-chloroprop-1-yl-3-yl.
  • Alkylene groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 10 C-atoms, in particular 1 to 6 C-atoms or preferably 2 to 4 C-atoms, as well as the appropriate unsaturated and / or substituted remainders in Carbon skeleton, which can each be straight-chain or branched. Examples are methylene, ethylene, n- and i-propylene and n-, s-, i-, t-butylene.
  • Hydroxyalkyl groups in these residues are the lower carbon skeletons, e.g. B. with 1 to 6 carbon atoms, in particular 1 to 4 carbon atoms, and the corresponding unsaturated and / or substituted radicals in the carbon skeleton, which may each be straight-chain or branched. Examples of these are 1, 2-dihydroxyethyl and 3-hydroxypropyl.
  • Halogen is fluorine, chlorine, bromine or iodine.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, CF 3 CF 2 O, OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
  • Aryl means a mono-, bi- or polycyclic aromatic system, for example phenyl or naphthyl, preferably phenyl.
  • compounds of the general formula (I) or their agrochemical salts or quaternary N derivatives of the invention are of particular interest, in which individual radicals are one of those already mentioned or mentioned below have preferred meanings, or in particular those in which one or more of the aforementioned or mentioned below preferred meanings occur in combination.
  • the present compounds of the general formula (I) have a chiral carbon atom, which is illustrated in the structure shown below by the label ( * ):
  • this carbon atom can have both an (R) and an (S) configuration.
  • the present invention relates to compounds of the general formula (I) having both (S) and (R) configurations, that is to say that the present invention covers the compounds of the general formula (I) in which the carbon atom in question
  • the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with ( * ) having a stereochemical purity of 60 to 100% (R), preferably 80 to 100% (R), in particular 90 to 100% (R), especially 95 to 100% (R).
  • the present invention relates in particular to compounds of the general formula (I) in which the stereochemical configuration at the carbon atom marked with (*) having a stereochemical purity of 60 to 100% (R, or analog-R), preferably 80 to 100 % (R, or analog-R), in particular 90 to 100% (R, or analog-R), very particularly 95 to 100% (R, or analog-R), is present.
  • the compounds of the general formula (I) according to the invention may have further chiral centers on the carbon atoms labeled with ( ** ) and (3):
  • diastereomers (Z and E isomers) can occur.
  • enantiomers and diastereomers may occur.
  • Corresponding stereoisomers can be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods. Similarly, stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants. The invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not specified with their specific stereoform and their mixtures.
  • a further subject of the present invention are processes for preparing corresponding compounds of the general formula (I) and / or salts thereof and / or their agrochemically compatible quaternized nitrogen derivatives: a.) For the preparation of compounds of the general formula (I)
  • R 1 and R 2 have the above meaning and Z 1 is an exchangeable radical or a leaving group, in particular chlorine, trichloromethyl, (Ci-C 4 ) alkylsulfonyl, unsubstituted or substituted phenyl (dC 4 ) alkylsulfonyl or (C 1 -C 4 ) -alkylphenylsulfonyl, with an amine of the general formula (III) or an acid addition salt thereof
  • the isomer mixture of (II) and (V) obtained in this way can be separated by chromatography or used as a mixture in the subsequent reaction.
  • amines of the general formula (III) or the acid addition salt thereof are commercially available or their synthesis is described in WO 2004/069814 A1.
  • the pyrimidines of the general formula (II) are commercially available; Special derivatives can be prepared by known methods. For example a. According to the publication by Perez et al., Synthesis 1983, p. 402, the corresponding 4-hydroxy-pyrimidines can be prepared from cyanoacetamide and N-cyanocarboximidoates, which are then subsequently exemplified with phosphorus oxychloride in the compounds of the general formula
  • R 2 or R 10 halogen, in particular iodine or bromine, with acetylenes or with trimethylsilyl-protected acetylene with transition metal catalysis, for example with bis (triphenylphosphine) - palladium (II) chloride, in protic or aprotic solvents and addition of base at temperatures between 20 and 150 0 C too
  • Alkoxyalkyl or aminoalkyl or diaminoalkyl be implemented. Collections of compounds of formula (I) and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
  • chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods.
  • solid phase assisted synthetic methods are well described in the literature, e.g. Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999.
  • the use of solid-phase assisted synthetic methods allows a number of protocols known from the literature, which in turn can be performed manually or automatically.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the methods described herein provides compounds of formula (I) and their salts in the form of substance collections called libraries.
  • the present invention also provides libraries containing at least two compounds of formula (I) and their salts.
  • Another object of the invention is due to the herbicidal property of the compounds of general formula (I), the use of the Compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants.
  • Herbicides are used in agricultural crops during various stages of cultivation. Thus, the application of some products already before or during the sowing. Others are applied before the crop is run up, i. before the seedling breaks through the earth's surface (pre-emergence herbicides). Postemergence herbicides are finally used when either the cotyledons or leaves are already formed from the crop.
  • the compounds of the invention can be used both in the forerun and in the wake, wherein a use of the compounds of the invention in the flow is preferred.
  • Pre-emergence treatment includes pre-sowing (ppi) pre-sowing treatment as well as treatment of sown, but not overgrown crop areas.
  • the compounds of the formula (I) according to the invention and their salts, also referred to below together as compounds of the formula (I), have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. Even difficult to control perennial weeds, which expel from rhizomes, rhizomes or other permanent organs, are well detected by the active ingredients. It does not matter whether the substances are applied in the pre-sowing, pre-emergence or postemergence process.
  • dicotyledonous weed species In dicotyledonous weed species, the spectrum of activity extends to species such. Galium, Viola, Veronica, Lamium, Stellaria, Amaranthus, Sinapis, Ipomoea, Matricaria, Abutilon and Sida on the annall side as well as Convolvulus, Cirsium, Rumex and Artemisia in perennial weeds.
  • herbicidal activity in dicotyledonous weeds such as Ambrosia, Anthemis, Carduus, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Emex, Galeopsis, Galinsoga,
  • the active compounds of the general formula (I) When the active compounds of the general formula (I) are applied to the green plant parts in the postemergence process, a drastic growth arrest also occurs very rapidly after the treatment and the weed plants remain in the growth stage present at the time of application or die completely after a certain time, so that This way, a weed competition that is harmful to cultivated plants is eliminated very early and sustainably.
  • the compounds of general formula (I) according to the invention have excellent herbicidal activity against mono- and dicotyledonous weeds, crops of economically important crops such. As wheat, barley, rye, rice, corn, sugar beet, cotton, oilseed rape and soy only insignificant or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in agricultural crops.
  • the substances of the general formula (I) according to the invention have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and to facilitate harvesting, such as, for example, B. be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of unwanted vegetative growth, without killing the plants. An inhibition of vegetative growth plays in many mono- and dicots
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds of general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants.
  • new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP 0221044, EP 0131624).
  • a) genetic modifications of crop plants were described for the purpose of modifying the starch synthesized in the plants (eg WO 92/011376, WO 92/014827, WO 91/019806), b) transgenic crop plants which are resistant to certain herbicides of the type glufosinate (cf., for example, EP 0242236, EP 0242246) or glyphosate (WO 92/000377) or the sulfonylureas (EP 0257993, US 5013659), c) transgenic crop plants, for example cotton, with the ability Bacillus thuringiensis Producing toxins (Bt toxins) which render the plants resistant to certain pests (EP 0142924, EP 0193259), d) transgenic modified fatty acid culture plants (WO 91/013972), e) genetically modified crops with new content or secondary substances z.
  • Bt toxins Bacillus thuringiensis Producing toxins
  • transgenic crops (F) genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398), g) transgenic crops, the pharmaceutically or diagnostically important proteins h) transgenic crops which are characterized by higher yields or better quality, i) transgenic crop plants which are characterized by a combination of, for example, the above new properties ("gene stacking").
  • nucleic acid molecules can be introduced into plasmids that allow mutagenesis or sequence alteration by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996.
  • the production of plant cells having a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA for the purpose of achieving a cosupressing effect or the expression of at least one corresponding thereto engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds of the general formula (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such as B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • the essential plant enzymes eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydroxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, resistant.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • the compounds of the general formula (I) can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions , Suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for litter and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • Injection powders are preparations which are uniformly dispersible in water and, in addition to the active ingredient, also contain ionic and / or nonionic surfactants (wetting agent, dispersant) in addition to a diluent or inert substance, eg.
  • the herbicidal active compounds for example, in conventional apparatus such as hammer mills, blower mills and Finely ground air jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent z.
  • organic solvent z B. butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as, for example, B. Sorbitanfett Text- ester or Polyoxethylenensorbitanester such. B. Polyoxyethylensorbitanfett Text- ester.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate
  • nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide / ethylene oxide condensation products, alkyl polyethers,
  • Dusts are obtained by grinding the active ingredient with finely divided solids, eg. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids eg. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally added surfactants, such as. B. are already listed above in the other formulation types, are produced.
  • Emulsions eg. As oil-in-water emulsions (EW) can be, for example, by means of stirring, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, such as. B. are listed above in the other types of formulation produced.
  • EW oil-in-water emulsions
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying active substance concentrates by means of adhesives, for.
  • adhesives for.
  • polyvinyl alcohol polyacrylsaurem Sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired mixed with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • spray drying for the preparation of plate, fluidized bed, extruder and spray granules see, for. B. Methods in "Spray-Drying Handbook” 3rd Ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration”, Chemical and Engineering 1967, pages 147 ff; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of active compound of the formula (I).
  • the active ingredient concentration z. B. about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Dusty formulations contain 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% of active ingredient.
  • the active ingredient content depends in part on whether the active compound is liquid or solid and which granulating aids, fillers and the like are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvents, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and viscosity modifiers.
  • the compounds of the general formula (I) or salts thereof can be used as such or in the form of their preparations (formulations) with other pesticidal substances, such.
  • pesticidal substances such as insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or growth regulators combined.
  • combination partners for the compounds according to the invention in mixture formulations or in the tank mix for example, known active compounds which are based on an inhibition of, for example, acetylactate synthase, acetyl-CoA-Ca rboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase , p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase, Photosystem I 1 photosystem II, protoporphyrinogen oxidase are based, can be used, for example, as described in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 13th edition, The British Crop Protection Council and the Royal Soc.
  • herbicides or plant growth regulators which can be combined with the compounds according to the invention are the following active substances (the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with the chemical name or with the code number and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • ISO International Organization for Standardization
  • isomers such as stereoisomers and optical isomers.
  • the safeners are preferably selected from the group consisting of:
  • the safeners are preferably selected from the group consisting of: S1) compounds of the formula (S1),
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (C 1 -C 4) -alkyl, (Ci-C 4) alkoxy, nitro or (dC 4) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or unsaturated five-membered ring heterocycles having 1 to 3 hetero ring atoms from the group N and O, wherein at least one N atom and at most one O atom is contained in the ring, preferably a radical from the group (W A 1 ) to (W A 4 ),
  • n A is 0 or 1;
  • R A 2 is OR A 3 , SR A 3 or NRA 3 R A 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one N atom and up to 3 hetero atoms, preferably from the group O and S. which is connected via the N atom with the carbonyl group in (S1) and is unsubstituted or substituted by radicals from the group (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula ORA 3 , NHR A 4 or N (CH 3 ) 2 , in particular of the formula OR A 3 ;
  • RA 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RA 4 is hydrogen, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • RA 5 is H, (C 1 -C 8 ) alkyl, (C 1 -C 8 ) haloalkyl, (C 1 -C 4 ) alkoxy (C 1 -C 8 ) alkyl, cyano or COORA 9 , wherein R A 9 is hydrogen, (C 1 -C 8 ) alkyl , (Ci-C ⁇ ) haloalkyl, (C 1 - C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 6) hydroxyalkyl, (C 3 -C 12) cycloalkyl or tri- (C r C 4 ) -alkyl-silyl; RA 6 , RA 7 , RA 8 are identical or different hydrogen, (Ci-C 8 ) alky
  • R 6 1 is halogen, (C 1 -C 4 ) AIKyI, (Ci-C 4 ) alkoxy, nitro or (C r C 4 ) haloalkyl;
  • n B is a natural number from 0 to 5, preferably 0 to 3;
  • RB 2 is OR 8 3 , SR B 3 or NR 6 3 RB 4 or a saturated or unsaturated 3- to 7-membered heterocycle having at least one
  • N atom and up to 3 heteroatoms preferably from the group O and S, which is connected via the N atom to the carbonyl group in (S2) and unsubstituted or by radicals from the group (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy or optionally substituted phenyl, preferably a radical of the formula OR B 3 , NHR 6 4 or N (CH 3 ) 2 , in particular of the formula OR B 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 C atoms;
  • RB 4 is hydrogen, (C 1 -C 6 alkyl, (C 1 -C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • T B is a (C 1 or C 2 ) alkanediyl chain which is unsubstituted or substituted by one or two (C 1 -C 4 ) Alkyl radicals or is substituted by [(CrCaJ-alkoxyJ-carbonyl;
  • S2 a Compounds of the 8-quinolinoxyacetic acid (S2 a), preferably (5-chloro-8-quinolinoxy) ester acetic acid, ethyl (1-methylhexyl) ( “cloquintocet-mexyl”) (S2-1),
  • EP-A-191 736 or EP-AO 492 366 as well as (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium , Magnesium, aluminum, iron,
  • Rc 1 is (C r C4) alkyl, (Ci-C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 - C 7 ) cycloalkyl, preferably dichloromethyl;
  • Rc 2, rc 3 are identical or different hydrogen, (Ci-C 4) alkyl, (C 2 -C 4) alkenyl,
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) of
  • X 0 is CH or N;
  • RD 1 is CO-NRD 5 RD 6 or NHCO-R 0 7 ;
  • RD 2 is halogen, (dC 4) haloalkyl, (Ci-C 4) haloalkoxy, nitro, (C 1 -C 4) AIKyI, (Ci-C 4) alkoxy, (Ci-C 4) alkylsulfonyl, (Ci-C 4) alkoxycarbonyl or (C -C 4) alkylcarbonyl!;
  • R D 3 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R 0 4 is halogen, nitro, (C r C 4 ) alkyl, (C r C 4 ) haloalkyl, (C 1 -C 4 ) haloalkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (C 1 -C 4 ) -alkoxy, cyano, (Ci-C 4) alkylthio, (C r C4) alkylsulfinyl, (CrC ⁇ alkylsulfonyl, (C 1 -C 4) alkoxycarbonyl or (C 1 -C 4) alkylcarbonyl;
  • R D 5 is hydrogen, (C 1 -C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 -C 6 ) cycloalkenyl, Phenyl or 3- to 6-membered heterocyclyl containing
  • V 0 heteroatoms from the group of nitrogen, oxygen and sulfur where the seven last-mentioned radicals are represented by v D substituents from the group consisting of halogen, (C 1 -C 6 ) alkoxy, (C 1 -C 6 ) halogenoalkoxy, (C 1 -C 2 ) alkylsulfinyl, (C 1 -C 2 ) alkylsulfonyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 -alkoxycarbonyl, (C 1 -C 4 ) -alkylcarbonyl and phenyl and in the case of cyclic radicals also (C 1 -C 4 ) -alkyl and (C - ⁇ -C 4 ) haloalkyl are substituted;
  • RD 6 is hydrogen, (C 1 -C 4 ) alkyl, (C 2 -C 6 ) alkenyl or (C 2 -C 6 ) alkynyl, where the three latter radicals are represented by v D radicals from the group consisting of halogen, hydroxy, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy and (C 1 -C 4 ) alkylthio, or R 0 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
  • R D 7 is hydrogen, (Ci-C 4) alkylamino, di- (C 1 -C 4) alkylamino, (C r C6) alkyl,
  • (C 3 -C 6 ) cycloalkyl where the 2 latter radicals by v D substituents alkoxy, (Ci-C ⁇ JHaloalkoxy and (CrC 4) alkylthio and in case of cyclic radicals, also (Ci-C 4) alkyl and (C- ⁇ -C 4) haloalkyl substituted from the group halogen, (4 Ci-C); is O, 1 or 2;
  • ⁇ ID is 1 or 2;
  • VD is O, 1, 2 or 3;
  • RD 4 is halogen, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3; (TID 1 or 2; VD is O, 1, 2 or 3;
  • Acylsulfamoylbenzoeklareamide for example, the following formula (S4 b ), for example, are known from WO-A-99/16744,
  • R 0 8 and R 0 9 independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 6 ) -alkenyl, (C 3 -C 6 ) -alkynyl,
  • R 0 4 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 m D is 1 or 2;
  • RE 1 are independently halogen, (Ci-C 4) alkyl, (Ci-C 4) alkoxy,
  • RE 3 are independently hydrogen, (Ci-C 4) alkyl, (C 2 - C 6) alkenyl, (C 2 -C 4) alkynyl, cyanoalkyl, (dC 4) haloalkyl, phenyl,
  • n E 1 is 0 or 1
  • ⁇ IE 2 , ⁇ E 3 are each independently 0, 1 or 2, preferably: diphenylmethoxyacetic acid,
  • RF 1 is halogen, (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) alkoxy, (C 1 -C 4) HaIOaIkOXy,
  • R F 2 is hydrogen or (C r C 4 ) alkyl
  • R F 3 is hydrogen, (Ci-C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy are substituted, or their salts,
  • XF CH, ⁇ F is an integer from 0 to 2
  • RF 1 is halogen, (C r C4) alkyl, (CrC 4) haloalkyl, (Ci-C 4) alkoxy, (C 1 -C 4) HaIOaIkOXy,
  • RF 2 is hydrogen or (C r C 4 ) alkyl
  • RF 3 is hydrogen, (Ci-C ⁇ ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, wherein each of the aforementioned C-containing radicals unsubstituted or by one or more, preferably to to three equal or different residues from the
  • R G 1 is halogen, (C r C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
  • Y G , ZG independently of one another are O or S, nc is an integer from 0 to 4,
  • R G 2 (C 1 -C 6 ) AIKyI, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl,
  • RG 3 is hydrogen or (Ci-C 6 ) alkyl.
  • S11) oxyimino compound type compounds (S11) known as seed dressings such as those described in US Pat. B.
  • Oxabetrinil ((Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S11-1), which is known as a seed dressing safener for millet against damage by metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-1-ethanone-O- (1,3-dioxolan-2-ylmethyl) -oxime) (S11-2), which is used as a seed dressing Safener for millet is known against damage from metolachlor, and
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S11-3), which is known as a seed dressing safener for millet against damage by metolachlor.
  • S12 Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
  • S12 Isothiochromanone (S12) class agents, e.g. Methyl - [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS No. 205121-04-6) (S12-1) and related compounds of WO-A -1998 / 13361.
  • S13 One or more compounds from group (S13): "Naphthalene anhydride” (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed safener for corn against damage by thiocarbamate herbicides.
  • “Flurazole” (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage by alachlor and metachachlor, "CL 304415 "(CAS Reg. No. 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) of the company
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn, " MG-838 "(CAS Reg. No. 133993-74-5)
  • Some of the safeners are already known as herbicides and therefore, in addition to the herbicidal effect on harmful plants, also have a protective effect on the crop plants.
  • the weight ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the formula (I) or mixtures thereof with further herbicides / pesticides and provided and used as finished formulation or tank mixture with the herbicides.
  • the formulations present in commercial form are optionally diluted in the usual way, for.
  • the type of herbicide used u.a. varies the required application rate of the compounds of general formula (I). It can vary within wide limits, eg. B. between 0.001 and 10.0 kg / ha or more active substance, but it is preferably between 0.005 and 5 kg / ha.
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts,
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3% by weight.
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a compound of formula (I) and / or salts thereof 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin mixed on one Grinds pin mill and the powder granulated in a fluidized bed by spraying water as Granulier crampkeit.
  • a water-dispersible granule is also obtained by reacting 25 parts by weight of a compound of the formula (I) and / or its salts,
  • Herbicidal action or crop plant compatibility in pre-emergence Seeds of monocotyledonous or dicotyledonous weed or crop plants are laid out in sandy loam in wood fiber pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with addition of 0.2% wetting agent applied.
  • ABUTH Abutilon theophrasti
  • ALOMY Alopecurus myosuroides
  • AMARE Amaranthus retroflexus
  • CHEAL Chenopodium album
  • ECHCG Echinochloa crus-galli
  • POLCO Polygonum convolvulus
  • PHBPU Pharitis purpurea
  • SETVI Setaria viridis STEM: Stellaria media VERPE: Veronica persica VIOTR: Viola tricolor
  • compounds of the invention have a good herbicidal pre-emergence activity against a broad spectrum of grass weeds and weeds.
  • the compounds of Table 1 have very good herbicidal activity against harmful plants such as Stellaria media, Echinochloa crus-galli, Lolium multiflorum, Setaria viridis, Amaranthus retroflexus and Alopecurus myosuroides pre-emergence at an application rate of 0.32 kg and less active ingredient per hectare.
  • compounds according to the invention have a good herbicidal postemergence activity against a broad spectrum of grass weeds and weeds.
  • the compounds of Table 2 have very good herbicidal activity against harmful plants such as Echinochloa crus-galli, Abutilon theophrasti, Amaranthus retroflexus postemergence at an application rate of 0.32 kg and less active ingredient per hectare.

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Abstract

L'invention concerne des dérivés de pyrimidine et leur utilisation pour lutter contre la croissance indésirable de plantes. L'invention concerne des composés de formule générale (I) et leur utilisation dans le domaine de la protection des plantes.
PCT/EP2009/009287 2000-12-30 2009-12-28 Dérivés de pyrimidine et leur utilisation pour lutter contre la croissance indésirable de plantes WO2010076009A1 (fr)

Priority Applications (7)

Application Number Priority Date Filing Date Title
AU2009335286A AU2009335286A1 (en) 2008-12-30 2009-12-28 Pyrimidine derivatives and the use thereof for combating undesired plant growth
CA2748577A CA2748577A1 (fr) 2008-12-30 2009-12-28 Derives de pyrimidine et leur utilisation pour lutter contre la croissance indesirable de plantes
EP09799289.5A EP2384322B1 (fr) 2008-12-30 2009-12-28 Dérivés de pyrimidine et leur utilisation pour combattre la croissance indésirable de plantes
JP2011543990A JP5826633B2 (ja) 2008-12-30 2009-12-28 ピリミジン誘導体および望ましくない植物生長と闘うためのこれらの使用
MX2011006278A MX2011006278A (es) 2008-12-30 2009-12-28 Derivados de pirimidina y su utilizacion para la represion de un crecimiento indeseado de plantas.
BRPI0923893-0A BRPI0923893B1 (pt) 2000-12-30 2009-12-28 derivados de pirimidina opticamente ativos, seu uso e seu processo de preparação, composição herbicida ou reguladora do crescimento de plantas, e processo para controle de plantas nocivas ou para regular o crescimento de plantas
CN200980153524.1A CN102272107B (zh) 2008-12-30 2009-12-28 嘧啶衍生物及其用于抵抗不希望的植物生长的用途

Applications Claiming Priority (2)

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EP08022522.0 2008-12-30
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WO2018184978A1 (fr) 2017-04-05 2018-10-11 Bayer Cropscience Aktiengesellschaft Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices
US10183914B2 (en) 2014-07-01 2019-01-22 Bayer Cropscience Aktiengesellschaft 2-amino-5-keto-pyrimidine derivatives and the use thereof for controlling undesired plant growth
US10251395B2 (en) 2015-07-24 2019-04-09 Bayer Cropscience Aktiengesellschaft Substituted furano-/thienocycloalkylamino-2-pyrimidine derivatives and use thereof for controlling undesired plant growth
US10806142B2 (en) 2015-12-21 2020-10-20 Bayer Cropscience Aktiengesellschaft 2-amino-5-ketoxime-pyrimidine derivatives and their use for controlling undesired plant growth

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WO2013144187A1 (fr) 2012-03-29 2013-10-03 Bayer Intellectual Property Gmbh Dérivés de 5-aminopyridine et utilisation desdits dérivés pour la lutte contre la croissance de plantes indésirables
JP2015516383A (ja) * 2012-03-29 2015-06-11 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ ５−アミノピリミジン誘導体及び望ましくない植物の成長を防除するためのそれらの使用
US9375002B2 (en) 2012-03-29 2016-06-28 Bayer Intellectual Property Gmbh 5-aminopyrimidine derivatives and use thereof for combating undesired plant growth
US10183914B2 (en) 2014-07-01 2019-01-22 Bayer Cropscience Aktiengesellschaft 2-amino-5-keto-pyrimidine derivatives and the use thereof for controlling undesired plant growth
US10251395B2 (en) 2015-07-24 2019-04-09 Bayer Cropscience Aktiengesellschaft Substituted furano-/thienocycloalkylamino-2-pyrimidine derivatives and use thereof for controlling undesired plant growth
US10806142B2 (en) 2015-12-21 2020-10-20 Bayer Cropscience Aktiengesellschaft 2-amino-5-ketoxime-pyrimidine derivatives and their use for controlling undesired plant growth
WO2018184978A1 (fr) 2017-04-05 2018-10-11 Bayer Cropscience Aktiengesellschaft Dérivés de 2-amino-5-oxyalkyl-pyrimidine et leur utilisation pour lutter contre la croissance de plantes adventices
US11477982B2 (en) 2017-04-05 2022-10-25 Bayer Cropscience Aktiengesellschaft 2-amino-5-oxyalkyl-pyrimidine derivatives and their use for controlling undesired plant growth

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BRPI0923893B1 (pt) 2021-03-09
JP5826633B2 (ja) 2015-12-02
BRPI0923893A2 (pt) 2020-08-11
AR074921A1 (es) 2011-02-23
JP2012514016A (ja) 2012-06-21
CA2748577A1 (fr) 2010-07-08
EP2384322B1 (fr) 2014-08-27
EP2384322A1 (fr) 2011-11-09
AU2009335286A1 (en) 2011-07-21
KR20110102482A (ko) 2011-09-16
EP2206703A1 (fr) 2010-07-14
WO2010076009A8 (fr) 2011-06-23
TW201034572A (en) 2010-10-01
US8445408B2 (en) 2013-05-21

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